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Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione

Paper ID Volume ID Publish Year Pages File Format Full-Text
40718 45863 2012 6 PDF Available
Title
Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
Abstract

In this paper we have studied the liquid-phase enantioselective hydrogenation of 3,4-hexanedione using Pt-based catalysts, modified with chiral organotin compounds derived from the (−)-menthyl group: (−)-Pt-MenSnBu3 and (−)-Men3Sn-Sn-(−)-Men3. The organotin chiral modifiers were carefully synthesized and characterized in order to obtain optically pure compounds.The catalysts were prepared through a controlled surface reaction between the supported transition metal and the organometallic compound, using techniques derived from Surface Organometallic Chemistry on Metals (SOMC/M). The organobimetallic catalytic systems were found to be active and enantioselective in the hydrogenation of 3,4-hexanedione, yielding an enantiomeric excess of 25–27% for 4-hydroxy-3-hexanone.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (92 K)Download as PowerPoint slideHighlights► Organotin compounds with the chiral carbon bonded to the Sn exert a chiral induction. ► PtSn catalysts were obtained by a surface reaction between Pt and menthyl compounds. ► PtSn systems have been active in the liquid phase hydrogenation of 3,4-hexanedione. ► PtSn catalysts have been enantioselective (ee% for 4-hydroxy-3-hexanone of 25%). ► An increase in the ee% with a decrease in the reaction temperature has been observed.

Keywords
Enantioselectivity; 3,4-Hexanedione; Hydrogenation; (−)-Menthyl derivatives; PtSn; SOMC/M
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Pt-based chiral organotin modified heterogeneous catalysts for the enantioselective hydrogenation of 3,4-hexanedione
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volumes 445–446, 28 November 2012, Pages 209–214
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us